Structure and Reactivity of Glycosyl Isocyanides.

3D structural information was obtained from mono-, di- and trisaccharide formamide and isocyanide derivatives by analysis of their X-ray crystal structure and NMR spectroscopy. The isocyanide anomeric effect was observed. Data mining of the Cambridge Structural Database (CSD) was performed and statistically confirmed our findings. Application of the glycoside isocyanides in the synthesis of novel glycoconjugates as drug-like scaffolds by MCR chemistry underscores the usefulness of the novel building blocks.

[1]  I. Jerić,et al.  Synthesis of Glycomimetics by Diastereoselective Passerini Reaction. , 2018, The Journal of organic chemistry.

[2]  B. G. Davis,et al.  Studying glycobiology at the single-molecule level , 2018, Nature Reviews Chemistry.

[3]  T. Holak,et al.  Two-Step Synthesis of Complex Artificial Macrocyclic Compounds. , 2017, Angewandte Chemie.

[4]  Zai-Qun Liu,et al.  2-Isocyano glucose used in Ugi four-component reaction: An approach to enhance inhibitory effect against DNA oxidation. , 2017, European journal of medicinal chemistry.

[5]  Hong Chen,et al.  Modular synthesis of glycopolymers with well-defined sugar units in the side chain via Ugi reaction and click chemistry: hetero vs. homo , 2016 .

[6]  I. Bruno,et al.  Cambridge Structural Database , 2002 .

[7]  C. Hulme,et al.  One-Pot Two-Step Multicomponent Process of Indole and Other Nitrogenous Heterocycles or Amines toward α-Oxo-acetamidines. , 2016, Organic letters.

[8]  Eberhardt Herdtweck,et al.  Leuckart-Wallach Route Toward Isocyanides and Some Applications. , 2015, ACS combinatorial science.

[9]  A. Dömling,et al.  Leuckart–Wallach Approach to Sugar Isocyanides and Its IMCRs , 2015, Synthesis.

[10]  Constantinos G. Neochoritis,et al.  Efficient isocyanide-less isocyanide-based multicomponent reactions. , 2015, Organic letters.

[11]  A. Khalafi‐Nezhad,et al.  Carbohydrates as a reagent in multicomponent reactions: one-pot access to a new library of hydrophilic substituted pyrimidine-fused heterocycles. , 2014, Organic & biomolecular chemistry.

[12]  T. Rao,et al.  Four-Component, One-Pot Synthesis of N-Alkyl-4-oxo-3-phenylhexahydro-4H-spiro{[1,3]dioxolo[4′,5′:4,5]furo[2,3-f][1,2,3]triazolo[1,5-a][1,4]diazepine-9,1′-cyclohexane}-6-carboxamide Derivatives , 2014, Synthesis.

[13]  X. García‐Mera,et al.  Ugi-based approaches to quinoxaline libraries. , 2014, ACS combinatorial science.

[14]  Yufen Zhao,et al.  Novel syntheses of aryl quinoxaline C-nucleoside analogs by mild and efficient three-component sequential reactions. , 2014, Chemical communications.

[15]  C. Hulme,et al.  Bifunctional building blocks in the Ugi-azide condensation reaction: a general strategy toward exploration of new molecular diversity. , 2013, Organic & biomolecular chemistry.

[16]  G. Terraneo,et al.  Multi-component synthesis of peptide-sugar conjugates. , 2013, Organic & biomolecular chemistry.

[17]  Dong-Jun Kim,et al.  A Multinational, Observational Study to Investigate the Efficacy, Safety and Tolerability of Acarbose as Add-On or Monotherapy in a Range of Patients: The GlucoVIP Study , 2013, Clinical Drug Investigation.

[18]  M. Takeda,et al.  Conformational analysis of an extracellular polysaccharide produced by Sphaerotilus natans. , 2012, Carbohydrate research.

[19]  T. Rao,et al.  A novel sugar based intramolecular Ugi 3CC for the N -alkyl-3-oxo-4-aryl-octahydrofuro[2,3- f ][1,4]oxazepine-5-carboxamides , 2012 .

[20]  C. Hulme,et al.  Ugi/Robinson-Gabriel reactions directed toward the synthesis of 2,4,5-trisubstituted oxazoles. , 2012, Tetrahedron letters.

[21]  T. Holak,et al.  Exhaustive Fluorine Scanning toward Potent p53–Mdm2 Antagonists , 2012, ChemMedChem.

[22]  H. Kotsuki,et al.  Anomeric Effect of the Nitrogen Atom in the Isocyano and Urea Groups , 2010 .

[23]  J. Frampton.  Mifamurtide: a review of its use in the treatment of osteosarcoma. , 2010, Paediatric drugs.

[24]  N. Grenouillat,et al.  Lipid analogs of the nodulation factors using the Ugi/Passerini multicomponent reactions: preliminary studies on the carbohydrate monomer , 2007 .

[25]  Alexander Dömling,et al.  Recent developments in isocyanide based multicomponent reactions in applied chemistry. , 2006, Chemical reviews.

[26]  B. Westermann,et al.  Synthesis of multivalent aminoglycoside mimics via the Ugi multicomponent reaction. , 2005, Chemical communications.

[27]  J. Chisholm,et al.  Hydrogen bonding preference of equatorial versus axial hydroxyl groups in pyran and cyclohexane rings in organic crystals , 2005 .

[28]  Mattie S. M. Timmer,et al.  Carbohydrates as versatile platforms in the construction of small compound libraries , 2005 .

[29]  O. Lockhoff,et al.  Glycoconjugate libraries accessed by multicomponent reactions. , 2002, Combinatorial chemistry & high throughput screening.

[30]  T. Ziegler,et al.  PASSERINI AND UGI REACTIONS OF BENZYL AND ACETYL PROTECTED ISOCYANOGLUCOSES , 1999 .

[31]  O. Lockhoff.  An Access to Glycoconjugate Libraries through Multicomponent Reactions. , 1998, Angewandte Chemie.

[32]  Oswald Lockhoff.  Ein Zugang zu Glycokonjugat-Bibliotheken durch Mehrkomponentenreaktionen , 1998 .

[33]  T. Ziegler,et al.  PASSERINI AND UGI REACTIONS OF ANOMERIC GLUCOSYL ISONITRILES , 1998 .

[34]  P. Cintas,et al.  The structure of glycosyl amides: A combined study by NMR spectroscopy, X-ray crystallography, and computational chemistry , 1998 .